


Need for a New Secretary

by Destielssniper



Category: Supernatural
Genre: Anal Sex, Bottom Castiel, Boys Kissing, Crossdressing Castiel, Desk Sex, Light Bondage, M/M, Oblivious Dean, Older Man/Younger Man, Rough Sex, Smut, Tie Kink, Top Dean, Top Dean Smith, Twink Castiel
Language: English
Status: Completed
Published: 2017-05-13
Updated: 2017-05-13
Packaged: 2018-10-31 11:12:12
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,678
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10898148
Author URL: https://archiveofourown.org/users/Destielssniper/pseuds/Destielssniper
Summary: Dean Smith doesn't know why his secretaries keep quitting. Castiel tells him.





	Need for a New Secretary

Dean Smith had gone through many secretaries. None of them caught his eye. His last secretary quit because they didn’t like the job. He didn’t get why Anna quit. He was respectful to her and hardly yelled at her. When he did it was when he had a long day and he would apologize the next day.

Dean was looking through the list of people who wanted the job, they were mostly women he noticed when the door opened and a blue eyed man walked in. He looked a lot younger and smaller than Dean.

Dean looked back down at the paper and read through the younger man’s form. An eighteen-year-old with a weird name, Castiel Novak.

“Hello, Mr. Smith” Castiel’s voice broke through Dean’s trance. He cleared his throat and motioned for the younger man to sit down.

Castiel did obediently. His wide piercing blue eyes roamed over Dean’s body when the older man stood up to stand in front of the desk.

Dean felt those eyes and couldn’t suppress the shiver that went through his body. He shook himself out of it and turned his full attention to Castiel. The interview took longer than the others.

Dean didn’t know what it was but Castiel caught his eye. The younger man left after the interview and Dean sat down to make a call. He confirmed to his boss that he wanted to hire Castiel Novak as his secretary.

“I’m glad you have found someone suitable for the job Mr. Smith” Zachariah said before hanging up.

Dean never liked talking to that guy. Zachariah gave him a bad vibe. Nobody in this building like him but they were very successful because of him.

He made the final report about who was going to be his secretary before calling it a night. He grabbed his suit jacket and put it on. It was almost Winter and the temperature has been dropping.

He turned off the lights to his office and walked down the hallway to the elevator. He leaned his head back against the wall and closed his eyes. Another lonely night in his house.

-

A week later was when Castiel Novak started his first day of being Dean Smith’s secretary. When his boss walked into work he had his coffee ready for him. Dean gave him a polite smile and thanked him before going inside his office.

As usual, Dean didn’t ask much from his secretary just because he was stressing doesn’t mean he has to burden the others with it.

Castiel, on the other hand, didn’t mind. He didn’t mind at all. He liked taking orders from Dean. If only his boss would take a hint.

Dean is so oblivious about why his secretaries kept quitting. It was so simple. He’s a wealthy and sexy man. Everybody wanted to get fucked by him especially Castiel. It was a good thing he was very blunt about what he wanted.

After a few months of working for him. Castiel finally took the matter into his own hands.

Dean walked into work and, as usual, he greeted Castiel before walking into his office.

Castiel can feel the lace rubbing against his harden cock as he stood up and walked into Dean’s office.

Dean looked up in surprise “may I help you?” He asked.

“Yes, you may” Castiel replied and smirked a little.

Before Dean could say anything Castiel was walking up to him. He laid his hand on Dean’s chest and pushed him until he leaned back on the chair. He straddled him and played with his tie.

“Uh um” Dean stuttered and looked at Castiel with wide eyes then looked down at his tie.

“You’re very muscular” Castiel dragged his tongue against his bottom lip as he finally got to feel Dean’s arms. He liked it very much when his boss would take off his suit jacket. He could see how the dress shirt was tight on him showing his muscles.

“Castiel what are you doing?” Dean managed to let out when he found his voice. His cheeks were flushed and his eyes were looking anywhere but at the younger man on his lap.

“Isn’t it obvious Mr. Smith? Don’t you know why all your past secretaries have quit?” Castiel tilted his head as Dean shook his head, clueless. “They wanted you to fuck them and were very disappointed when you never made a move.”

Dean thought about his past secretaries. He knew some of them were flirting with him but he thought it was a joke. He never made a move because he didn’t want them to lose their job if they ever got caught.

Castiel got off of Dean’s lap and started to strip. He could feel the hungry gaze coming from the older man.

When he let his slacks pool around his ankles he heard the little sharp intake breath. Castiel smiled and turned around his back facing Dean. he sat back down on Dean’s lap and ground back.

“M-Mr. Smith” Castiel moaned.

Dean gripped his seat as lace rubbed against his crotch. He bit lip hard to keep from making noise. This was wrong on so many different levels that Dean hated the fact he felt himself growing hard. Castiel was his goddam secretary and eighteen years old. His breathing started to grow rapidly as the twink kept grinding back against him. If the little bastard didn’t stop now Dean would cum in his slacks.

Castiel laid his head back against Dean’s shoulder “come on touch me you’re allowed to.”

Dean hesitated for a bit before sliding his hand in between Castiel’s thighs and squeezing his harden cock.

Castiel let out a breathy whimper and bucked “is that all you got?” He knew he was testing his patience but he didn’t care at this point.

Dean gripped the twink’s hip with his other hand and stood up. He picked up Castiel and sat him on top of his desk. He slots himself in between the younger man’s legs and kissed him.

Castiel moaned into the kiss and wrapped his arms around Dean’s neck.

Dean pulled away from Castiel ignoring his whines “turn around, spread your legs, and put your hands behind your back.” He growled out his order.

Castiel scrambles to do as Dean told. When he was in position he felt Dean’s weight again.

Dean roamed his hands all over the lacy panties and black stockings his secretary had on. He grabbed the tie that was on the ground and slot it into Castiel’s mouth. Dean took off his own tie to bond Castiel’s wrists together.

Dean grabbed a lube and condom from his drawer. He had jerk off to the thought of Castiel a couple of times in his office. He would feel guilty after, but not now when he has Castiel under him and tied.

Dean uncapped the bottle and drizzled some lube on his fingers. He rubbed the cool liquid between his fingers to make it warm before sliding the panties aside to reveal the younger man’s hole. He pushed one finger in and groaned how tight Castiel was.

Castiel squeezed his eyes shut and bit on the tie that was in his mouth. He dug his fingernails into his palm as he felt the slight burn. Dean’s fingers were thicker than his and he loved it.

Dean added another when Castiel was loose enough. “You’re so tight I wonder how would you feel around my cock” his voice dropped even lower from the fog of lust that clouded his mind. He smirked at the sounds Castiel was making.

Dean prepped him until he was three fingers deep. He took out his fingers and unzipped his pants. He took out his hard thick cock and rolled on a condom. He positioned himself on Castiel’s hole and pushed in slowly.

Castiel pushed back and made frustrated sounds when Dean wouldn’t go any faster. He felt himself getting more stretched. Dean was bigger than he expected.

Dean gritted his teeth as he waited for Castiel to get used to his size and not pound into him. After a few minutes, Castiel was pushing back and moaning.

Dean pulled out and pushed back in slowly before growing bolder and picking up his pace. The desk scraped against the wooden floor as he pounded into the twink. His clothed chest rubbed against Castiel’s bareback.

“You feel so amazing” Dean grunted and gripped Castiel’s hair. It was getting harder to keep quiet when he kept going. It had been a while since he had fun like this. He didn’t know why he didn’t fuck this twink sooner.

Dean can feel Castiel clenching around his cock which made him groaned loudly. He shifted and thrust in roughly. He smirked when Castiel screamed knowing full well he had hit his prostate.

“There is it” Dean growled and kept hitting Castiel’s prostate. At this point, the younger man was sobbing. He couldn’t touch himself and his nipples were scraping against the desk mixing pain with pleasure.

A few more thrusts hitting his prostate made Castiel cum with a silent cry. Dean didn’t stop and kept thrusting into his plaint body. The older man moaned when Castiel clenched around him.

“Oh fuck!” Dean shouted when he came. He pulled out of Castiel and took off the condom. He tied it and threw it in the trash can. He tucked himself in before cleaning up.

Dean untied Castiel’s wrists and helped him put his clothes back on.

“Holy shit that was amazing” Castiel slurred a bit and stumbled, but Dean caught him before he could fall. Dean laid him down on the couch that was in his office.

“I can’t believe I just fucked you” Dean rubbed a hand over his face and sighed. He felt a hand touch his thigh and looked down at Castiel.

“It’s alright Dean I enjoyed it and I won’t tell anyone” Castiel gave him a small smile before closing his eyes.

“Well I’m glad” Dean chuckled when all he got was a snore in response.


End file.
